N000-{2-[2-(3-Methoxyphenyl)ethenyl]-phenyl}acetamide

Kartini Ahmad, Noel F. Thomas, Mohd Azlan Nafiah,

Khalijah Awang and Seik Weng Ng*

Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia

Correspondence e-mail: seikweng@um.edu.my

Received 5 May 2009; accepted 8 May 2009

Key indicators: single-crystal X-ray study; T = 100 K; mean �(C–C) = 0.003 A;

R factor = 0.052; wR factor = 0.140; data-to-parameter ratio = 17.3.

In the title compound, C17H17NO2, the phenylene rings are

bent with respect to the carbon–carbon double bond [dihedral

angle between rings = 39.6 (1)�]. The acetamido group is

twisted out of the plane of the aromatic ring [dihedral angle =

44.2 (1)�] in order to form an N–H� � �O hydrogen bond to the

acetamido group of an adjacent molecule, generating a zigzag

chain running along the c axis.

Related literature

The compound was synthesized in a study on indolostilbenes;

see: Ahmad et al. (2009).

Experimental

Crystal data

C17H17NO2

Mr = 267.32Monoclinic, P21=ca = 14.5588 (5) Ab = 10.3633 (4) Ac = 9.3667 (3) A� = 90.118 (1)�

V = 1413.22 (9) A3

Z = 4Mo K� radiation� = 0.08 mm�1

T = 100 K0.21 � 0.07 � 0.02 mm

Data collection

Bruker SMART APEXdiffractometer

Absorption correction: none12919 measured reflections

3236 independent reflections2036 reflections with I > 2�(I)Rint = 0.069

Refinement

R[F 2 > 2�(F 2)] = 0.052wR(F 2) = 0.140S = 1.013236 reflections187 parameters1 restraint

H atoms treated by a mixture ofindependent and constrainedrefinement

��max = 0.38 e A�3

��min = �0.25 e A�3

Table 1Hydrogen-bond geometry (A, �).

D—H� � �A D—H H� � �A D� � �A D—H� � �A

N1—H1� � �O1i 0.88 (1) 1.93 (1) 2.804 (2) 175 (2)

Symmetry code: (i) x;�yþ 32; z� 1

2.

Data collection: APEX2 software (Bruker, 2008); cell refinement:

SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to

solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to

refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics:

X-SEED (Barbour, 2001); software used to prepare material for

publication: publCIF (Westrip, 2009).

We thank the University of Malaya for supporting this

study.

Supplementary data and figures for this paper are available from theIUCr electronic archives (Reference: HG2514).

References

Ahmad, K., Thomas, N. F., Mukhtar, M. R., Noorbatcha, I., Faizal, W., Nafiah,J.-F., Azlan, M., Velu, S. S., Takeya, K., Morita, H., Lim, C.-G., Hadi, A. H.A. & Awang, K. (2009). Tetrahedron, 65, 1504–1516.

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin,

USA.Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.Westrip, S. P. (2009). publCIF. In preparation.

organic compounds

o1290 Ahmad et al. doi:10.1107/S1600536809017401 Acta Cryst. (2009). E65, o1290

Acta Crystallographica Section E

Structure ReportsOnline

ISSN 1600-5368

supplementary materials

supplementary materials

sup-1

Acta Cryst. (2009). E65, o1290 [ doi:10.1107/S1600536809017401 ]

N'-{2-[2-(3-Methoxyphenyl)ethenyl]phenyl}acetamide

K. Ahmad, N. F. Thomas, M. A. Nafiah, K. Awang and S. W. Ng

Comment

(type here to add)

Experimental

The compound was synthesized in a study on indolostilbenes (Ahmad et al., 2009). Crystals were grown from its solutionin ethyl acetate.

Refinement

Hydrogen atoms were placed at calculated positions (C–H 0.95–0.98 Å) and were treated as riding on their parent carbonatoms, with U(H) set to 1.2–1.5 times U~eq~(C). The amino H-atom was located in a difference Fourier map, and wasrefined with a distance restraint of N–H 0.88±0.01 Å; its temperature factor was refined.

Figures

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C17H17NO2 at the 70% probability level.Hydrogen atoms are drawn as spheres of arbitrary radius.

N'-{2-[2-(3-Methoxyphenyl)ethenyl]phenyl}acetamide

Crystal data

C17H17NO2 F000 = 568

Mr = 267.32 Dx = 1.256 Mg m−3

Monoclinic, P21/c Mo Kα radiationλ = 0.71073 Å

Hall symbol: -P 2ybc Cell parameters from 1682 reflectionsa = 14.5588 (5) Å θ = 2.4–27.7ºb = 10.3633 (4) Å µ = 0.08 mm−1

c = 9.3667 (3) Å T = 100 Kβ = 90.118 (1)º Plate, colorless

V = 1413.22 (9) Å3 0.21 × 0.07 × 0.02 mmZ = 4

supplementary materials

sup-2

Data collection

Bruker SMART APEXdiffractometer 2036 reflections with I > 2σ(I)

Radiation source: fine-focus sealed tube Rint = 0.069

Monochromator: graphite θmax = 27.5º

T = 100 K θmin = 1.4ºω scans h = −18→18Absorption correction: None k = −13→1312919 measured reflections l = −12→123236 independent reflections

Refinement

Refinement on F2 Secondary atom site location: difference Fourier map

Least-squares matrix: full Hydrogen site location: inferred from neighbouringsites

R[F2 > 2σ(F2)] = 0.052H atoms treated by a mixture ofindependent and constrained refinement

wR(F2) = 0.140 w = 1/[σ2(Fo

2) + (0.0657P)2 + 0.3754P]where P = (Fo

2 + 2Fc2)/3

S = 1.01 (Δ/σ)max = 0.001

3236 reflections Δρmax = 0.38 e Å−3

187 parameters Δρmin = −0.25 e Å−3

1 restraint Extinction correction: nonePrimary atom site location: structure-invariant directmethods

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq

O1 0.11400 (10) 0.71029 (14) 0.73510 (14) 0.0246 (4)O2 0.65965 (10) 0.58338 (15) 0.10659 (16) 0.0273 (4)N1 0.12402 (11) 0.66372 (17) 0.49961 (17) 0.0177 (4)H1 0.1185 (16) 0.699 (2) 0.4151 (15) 0.032 (7)*C1 0.14037 (13) 0.5285 (2) 0.5123 (2) 0.0172 (4)C2 0.08867 (14) 0.4550 (2) 0.6068 (2) 0.0204 (5)H2 0.0432 0.4955 0.6639 0.024*C3 0.10283 (14) 0.3241 (2) 0.6183 (2) 0.0243 (5)H3 0.0686 0.2749 0.6853 0.029*C4 0.16751 (15) 0.2639 (2) 0.5315 (2) 0.0269 (5)H4 0.1771 0.1734 0.5382 0.032*C5 0.21760 (14) 0.3364 (2) 0.4357 (2) 0.0236 (5)H5 0.2601 0.2941 0.3746 0.028*C6 0.20754 (13) 0.4707 (2) 0.4259 (2) 0.0185 (4)C7 0.10934 (13) 0.7448 (2) 0.6095 (2) 0.0187 (4)C8 0.08548 (16) 0.8812 (2) 0.5694 (2) 0.0257 (5)

supplementary materials

sup-3

H8A 0.1255 0.9410 0.6216 0.038*H8B 0.0213 0.8985 0.5941 0.038*H8C 0.0941 0.8931 0.4665 0.038*C9 0.26855 (14) 0.5474 (2) 0.3343 (2) 0.0208 (5)H9 0.2507 0.6338 0.3145 0.025*C10 0.34701 (14) 0.5057 (2) 0.2767 (2) 0.0222 (5)H10 0.3623 0.4177 0.2919 0.027*C11 0.41182 (14) 0.5822 (2) 0.1925 (2) 0.0206 (5)C12 0.38525 (15) 0.6915 (2) 0.1148 (2) 0.0242 (5)H12 0.3230 0.7191 0.1156 0.029*C13 0.45036 (16) 0.7595 (2) 0.0361 (2) 0.0261 (5)H13 0.4322 0.8334 −0.0168 0.031*C14 0.54070 (15) 0.7208 (2) 0.0343 (2) 0.0223 (5)H14 0.5844 0.7671 −0.0208 0.027*C15 0.56799 (14) 0.6138 (2) 0.1129 (2) 0.0218 (5)C16 0.50366 (14) 0.5444 (2) 0.1902 (2) 0.0212 (5)H16 0.5224 0.4701 0.2421 0.025*C17 0.69172 (16) 0.4821 (2) 0.1966 (2) 0.0302 (5)H17A 0.7586 0.4749 0.1882 0.045*H17B 0.6631 0.4005 0.1677 0.045*H17C 0.6755 0.5012 0.2959 0.045*

Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23

O1 0.0362 (9) 0.0232 (8) 0.0144 (7) 0.0009 (7) 0.0007 (6) −0.0012 (6)O2 0.0182 (8) 0.0272 (9) 0.0366 (9) −0.0019 (6) 0.0023 (6) 0.0044 (7)N1 0.0207 (9) 0.0181 (9) 0.0144 (8) 0.0017 (7) 0.0011 (7) 0.0019 (7)C1 0.0157 (10) 0.0204 (11) 0.0156 (9) 0.0000 (8) −0.0024 (8) −0.0020 (8)C2 0.0162 (10) 0.0245 (11) 0.0203 (10) 0.0016 (9) 0.0011 (8) 0.0000 (9)C3 0.0232 (12) 0.0231 (12) 0.0266 (11) −0.0028 (9) 0.0005 (9) 0.0043 (9)C4 0.0252 (12) 0.0170 (11) 0.0387 (13) −0.0006 (9) −0.0006 (10) −0.0002 (10)C5 0.0186 (11) 0.0227 (12) 0.0296 (11) 0.0013 (9) 0.0017 (9) −0.0028 (10)C6 0.0150 (10) 0.0210 (11) 0.0195 (10) −0.0009 (8) −0.0022 (8) −0.0026 (9)C7 0.0150 (10) 0.0214 (11) 0.0196 (10) −0.0007 (8) 0.0010 (8) −0.0007 (8)C8 0.0349 (13) 0.0208 (12) 0.0213 (10) 0.0048 (9) 0.0023 (9) −0.0014 (9)C9 0.0212 (11) 0.0190 (11) 0.0220 (10) 0.0008 (9) −0.0011 (8) −0.0008 (9)C10 0.0247 (12) 0.0197 (11) 0.0222 (10) 0.0001 (9) 0.0010 (9) −0.0009 (9)C11 0.0225 (11) 0.0233 (11) 0.0160 (9) −0.0030 (9) 0.0018 (8) −0.0051 (9)C12 0.0220 (11) 0.0268 (12) 0.0238 (11) 0.0020 (9) −0.0007 (9) −0.0017 (10)C13 0.0313 (13) 0.0237 (12) 0.0234 (11) −0.0005 (10) −0.0024 (9) 0.0028 (9)C14 0.0241 (12) 0.0215 (11) 0.0213 (10) −0.0055 (9) 0.0013 (8) 0.0016 (9)C15 0.0182 (11) 0.0254 (12) 0.0218 (10) −0.0016 (9) −0.0005 (8) −0.0055 (9)C16 0.0238 (11) 0.0194 (11) 0.0203 (10) 0.0004 (9) −0.0001 (8) −0.0007 (9)C17 0.0205 (12) 0.0338 (14) 0.0361 (13) −0.0009 (10) −0.0031 (10) 0.0052 (11)

Geometric parameters (Å, °)

O1—C7 1.231 (2) C8—H8B 0.9800

supplementary materials

sup-4

O2—C15 1.373 (2) C8—H8C 0.9800O2—C17 1.424 (3) C9—C10 1.336 (3)N1—C7 1.346 (3) C9—H9 0.9500N1—C1 1.426 (3) C10—C11 1.464 (3)N1—H1 0.877 (10) C10—H10 0.9500C1—C2 1.391 (3) C11—C16 1.394 (3)C1—C6 1.405 (3) C11—C12 1.400 (3)C2—C3 1.376 (3) C12—C13 1.393 (3)C2—H2 0.9500 C12—H12 0.9500C3—C4 1.393 (3) C13—C14 1.375 (3)C3—H3 0.9500 C13—H13 0.9500C4—C5 1.380 (3) C14—C15 1.388 (3)C4—H4 0.9500 C14—H14 0.9500C5—C6 1.402 (3) C15—C16 1.386 (3)C5—H5 0.9500 C16—H16 0.9500C6—C9 1.470 (3) C17—H17A 0.9800C7—C8 1.504 (3) C17—H17B 0.9800C8—H8A 0.9800 C17—H17C 0.9800

C15—O2—C17 117.48 (17) C10—C9—C6 125.4 (2)C7—N1—C1 125.17 (17) C10—C9—H9 117.3C7—N1—H1 114.4 (16) C6—C9—H9 117.3C1—N1—H1 120.2 (16) C9—C10—C11 126.5 (2)C2—C1—C6 120.73 (19) C9—C10—H10 116.7C2—C1—N1 120.06 (18) C11—C10—H10 116.7C6—C1—N1 119.19 (18) C16—C11—C12 118.93 (19)C3—C2—C1 120.6 (2) C16—C11—C10 118.36 (19)C3—C2—H2 119.7 C12—C11—C10 122.71 (19)C1—C2—H2 119.7 C13—C12—C11 119.8 (2)C2—C3—C4 119.8 (2) C13—C12—H12 120.1C2—C3—H3 120.1 C11—C12—H12 120.1C4—C3—H3 120.1 C14—C13—C12 120.7 (2)C5—C4—C3 119.6 (2) C14—C13—H13 119.6C5—C4—H4 120.2 C12—C13—H13 119.6C3—C4—H4 120.2 C13—C14—C15 119.9 (2)C4—C5—C6 121.8 (2) C13—C14—H14 120.0C4—C5—H5 119.1 C15—C14—H14 120.0C6—C5—H5 119.1 O2—C15—C16 124.12 (19)C5—C6—C1 117.31 (19) O2—C15—C14 115.96 (18)C5—C6—C9 120.78 (19) C16—C15—C14 119.9 (2)C1—C6—C9 121.83 (19) C15—C16—C11 120.7 (2)O1—C7—N1 122.77 (19) C15—C16—H16 119.6O1—C7—C8 121.59 (18) C11—C16—H16 119.6N1—C7—C8 115.64 (17) O2—C17—H17A 109.5C7—C8—H8A 109.5 O2—C17—H17B 109.5C7—C8—H8B 109.5 H17A—C17—H17B 109.5H8A—C8—H8B 109.5 O2—C17—H17C 109.5C7—C8—H8C 109.5 H17A—C17—H17C 109.5H8A—C8—H8C 109.5 H17B—C17—H17C 109.5H8B—C8—H8C 109.5

supplementary materials

sup-5

C7—N1—C1—C2 42.6 (3) C1—C6—C9—C10 162.9 (2)C7—N1—C1—C6 −138.9 (2) C6—C9—C10—C11 −175.99 (18)C6—C1—C2—C3 0.5 (3) C9—C10—C11—C16 154.0 (2)N1—C1—C2—C3 178.97 (18) C9—C10—C11—C12 −25.9 (3)C1—C2—C3—C4 −2.0 (3) C16—C11—C12—C13 0.5 (3)C2—C3—C4—C5 0.7 (3) C10—C11—C12—C13 −179.63 (19)C3—C4—C5—C6 2.1 (3) C11—C12—C13—C14 −0.2 (3)C4—C5—C6—C1 −3.5 (3) C12—C13—C14—C15 −0.9 (3)C4—C5—C6—C9 173.33 (19) C17—O2—C15—C16 −6.6 (3)C2—C1—C6—C5 2.2 (3) C17—O2—C15—C14 174.07 (18)N1—C1—C6—C5 −176.28 (18) C13—C14—C15—O2 −179.00 (19)C2—C1—C6—C9 −174.62 (18) C13—C14—C15—C16 1.7 (3)N1—C1—C6—C9 6.9 (3) O2—C15—C16—C11 179.34 (19)C1—N1—C7—O1 4.4 (3) C14—C15—C16—C11 −1.4 (3)C1—N1—C7—C8 −174.86 (18) C12—C11—C16—C15 0.3 (3)C5—C6—C9—C10 −13.8 (3) C10—C11—C16—C15 −179.58 (18)

Hydrogen-bond geometry (Å, °)

D—H···A D—H H···A D···A D—H···A

N1—H1···O1i 0.88 (1) 1.93 (1) 2.804 (2) 175 (2)Symmetry codes: (i) x, −y+3/2, z−1/2.

supplementary materials

sup-6

Fig. 1